Benzylamine → N-benzyl-3-[4-(2-(cyclopropylmethoxy)ethyl)phenoxy]-2-hydroxypropylamine

HRID 1906673Notes

Reaction equation

HRID 1906673 reaction equation
[CH:1]1([CH2:4][O:5][CH2:6][CH2:7][C:8]2[CH:18]=[CH:17][C:11]([O:12][CH2:13][CH:14]3[O:16][CH2:15]3)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)CC>[CH2:19]([NH:26][CH2:15][CH:14]([OH:16])[CH2:13][O:12][C:11]1[CH:17]=[CH:18][C:8]([CH2:7][CH2:6][O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[CH:9][CH:10]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 117915422-((4-(2-(Cyclopropylmethoxy)ethyl)phenoxy)methyl)oxirane

Product 1

HCID 14025301N-benzyl-3-[4-(2-(cyclopropylmethoxy)ethyl)phenoxy]-2-hydroxypropylamineYield 61.5%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

1-[4-(2-Cyclopropylmethoxyethyl)phenoxy]-2,3-epoxypropane (10 g) and benzylamine (13 g) were stirred under reflux, in n-propanol (100 ml) for 20 hours. The mixture was cooled and evaporated under reduced pressure to give a residue. This was stirred under petroleum ether (60°-80°) for 30 minutes; the solvent was decanted and the residue triturated with further petroleum ether. A white solid was obtained, collected by filtration and recrystallised from acetonitrile to afford N-benzyl-3-[4-(2-(cyclopropylmethoxy)ethyl)phenoxy]-2-hydroxypropylamine (8.8 g), m.p. 75°-6° C.

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated under reduced pressure
  3. customto give a residue
  4. customthe solvent was decanted
  5. customthe residue triturated with further petroleum ether
  6. customA white solid was obtained
  7. filtrationcollected by filtration
  8. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-91bfe3a9595b41ce987b83c777549f16
Source dataset
uspto-grants-1987_03
Patent number
US04652563

Reaction notes

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